Dichloromethane → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

HRID 418578

반응식

HRID 418578 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=3)[S:10][C:3]=12.[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[OH:27].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[O:27][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=3)[S:10][C:3]=12

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 222500727-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

생성물 1

HCID 666494047-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine수율 43%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

반응 조건

온도
190 °C

실험 절차

A mixture of the compound 16 (1.52 g, 6.09 mmol), 2-fluoro-4-nitrophenol (3.87 g, 24.6 mmol) and K2CO3 (4.31 g, 31.2 mmol) in Ph2O (20 mL) was heated at 190° C. overnight. DCM (250 mL) was added to the resultant dark-brown mixture, which was then extracted with aqueous 1M HCl. The aqueous layer was collected, washed with DCM and basified with NH4OH. The resultant cloudy mixture was extracted with DCM. The organic phase was combined, filtered; the filtrate was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resultant yellow solid was purified by flash chromatography, eluent EtOAc/MeOH (80:20) to afford title-compound 17 as a yellow solid (0.96 g, 43% yield). MS (m/z): 371.0 (M+H).

후처리

  1. extractionwas then extracted with aqueous 1M HCl
  2. customThe aqueous layer was collected
  3. washwashed with DCM and basified with NH4OH
  4. extractionThe resultant cloudy mixture was extracted with DCM
  5. filtrationfiltered
  6. washthe filtrate was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant yellow solid was purified by flash chromatography, eluent EtOAc/MeOH (80:20)

출처 및 근거

ORD 기록
ord-9904b252538b44fbb42d51e07b9c4a52
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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